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The title compound, C19H23NSi2, is a TMS-protected rigid-rod di-yne. It is useful as a model compound for organometallic species of which it is a precursor and, like them, exhibits π-conjugation through the heteroaromatic linker unit in the backbone. The mol­ecule is pseudo-linear, with a planar central quinoline group. Two C—H...N short intermolecular contacts are found, with C...N distances of 3.483 (5) and 3.671 (6) Å. An intermolecular contact between an aromatic H atom and the C[triple bond]C triple bond is also observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018184/cf6215sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018184/cf6215Isup2.hkl
Contains datablock I

CCDC reference: 200759

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.083
  • wR factor = 0.225
  • Data-to-parameter ratio = 15.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
DIFF_020 Alert A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF_022 Alert A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity.
Amber Alert Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.18 From the CIF: _reflns_number_total 3166 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3526 Completeness (_total/calc) 89.79% Alert B: < 90% complete (theta max?)
Author response: The data was collected on a one-circle phi diffractometer with two different orientations of the crystal. Despite this attempt to cover all of reciprocal space only just under 90% could be accessed to a 2\q~max~ of 50.0\%.

Yellow Alert Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(5) - C(10) = 1.45 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(8) - C(15) = 1.44 Ang.
2 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: R-AXIS IIc Control Software (Rigaku/MSC, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C19H23NSi2F(000) = 688
Mr = 321.56Dx = 1.091 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.334 (2) ÅCell parameters from 4490 reflections
b = 10.604 (2) Åθ = 3.8–25.2°
c = 12.465 (2) ŵ = 0.18 mm1
β = 104.96 (1)°T = 180 K
V = 1958.1 (5) Å3Block, colourless
Z = 40.3 × 0.3 × 0.25 mm
Data collection top
Rigaku R-AXIS IIc
diffractometer
Rint = 0.067
φ scansθmax = 25.2°, θmin = 3.8°
5136 measured reflectionsh = 1817
3166 independent reflectionsk = 120
2003 reflections with I > 2σ(I)l = 014
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.083 w = 1/[σ2(Fo2) + (0.1197P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.225(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.47 e Å3
3166 reflectionsΔρmin = 0.36 e Å3
205 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.74685 (7)0.24344 (10)0.28418 (9)0.0433 (4)
Si21.38795 (7)0.23895 (11)0.47410 (10)0.0466 (4)
N11.0759 (2)0.0595 (3)0.2498 (3)0.0444 (8)
C11.0084 (3)0.0204 (4)0.2346 (3)0.0473 (10)
H11.01090.0830.28980.057*
C20.9329 (3)0.0199 (4)0.1425 (3)0.0488 (10)
H20.88710.0820.13520.059*
C30.9265 (3)0.0713 (4)0.0640 (3)0.0414 (9)
H30.87580.07390.00140.05*
C40.9958 (2)0.1619 (4)0.0762 (3)0.0394 (9)
C50.9953 (3)0.2582 (3)0.0029 (3)0.0382 (9)
C61.0666 (3)0.3421 (4)0.0132 (3)0.0513 (11)
H61.06590.40680.03970.062*
C71.1397 (3)0.3321 (4)0.1071 (4)0.0523 (11)
H71.18830.39010.11640.063*
C81.1430 (2)0.2413 (3)0.1855 (3)0.0396 (9)
C91.0710 (2)0.1522 (3)0.1717 (3)0.0395 (9)
C100.9196 (3)0.2652 (4)0.0999 (3)0.0444 (10)
C110.8533 (3)0.2619 (4)0.1773 (3)0.0435 (10)
C120.6786 (4)0.1285 (5)0.2296 (5)0.0807 (16)
H12A0.6190.12030.28180.121*
H12B0.7090.04640.22020.121*
H12C0.67170.15780.15760.121*
C130.6896 (4)0.3981 (5)0.3067 (6)0.093 (2)
H13A0.63670.39270.37050.139*
H13B0.67040.42180.24030.139*
H13C0.73140.46190.32130.139*
C140.7689 (3)0.1758 (5)0.4114 (4)0.0624 (13)
H14A0.71180.16670.46850.094*
H14B0.80920.23190.43870.094*
H14C0.79730.09290.39450.094*
C151.2192 (3)0.2345 (4)0.2817 (3)0.0448 (10)
C161.2846 (3)0.2355 (4)0.3601 (4)0.0501 (11)
C171.3996 (3)0.0863 (5)0.5491 (4)0.0737 (15)
H17A1.45630.08550.60750.111*
H17B1.34880.07550.58250.111*
H17C1.39970.01730.49680.111*
C181.3794 (4)0.3685 (5)0.5705 (4)0.0848 (17)
H18A1.43110.3650.63590.127*
H18B1.37920.44970.53290.127*
H18C1.32330.35950.59380.127*
C191.4825 (3)0.2640 (5)0.4100 (5)0.0753 (16)
H19A1.53940.26750.46820.113*
H19B1.48480.19410.35930.113*
H19C1.47360.34350.36860.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0398 (7)0.0476 (7)0.0382 (7)0.0038 (5)0.0022 (5)0.0031 (5)
Si20.0392 (7)0.0514 (7)0.0419 (7)0.0006 (5)0.0026 (5)0.0039 (5)
N10.055 (2)0.0413 (18)0.0376 (19)0.0084 (16)0.0124 (15)0.0021 (15)
C10.052 (2)0.049 (2)0.040 (2)0.001 (2)0.0105 (19)0.0104 (19)
C20.050 (2)0.048 (2)0.049 (3)0.0010 (19)0.0134 (19)0.006 (2)
C30.045 (2)0.044 (2)0.035 (2)0.0049 (17)0.0102 (16)0.0041 (17)
C40.044 (2)0.042 (2)0.032 (2)0.0054 (17)0.0088 (16)0.0051 (17)
C50.040 (2)0.042 (2)0.031 (2)0.0009 (16)0.0058 (15)0.0025 (17)
C60.056 (3)0.057 (3)0.036 (2)0.001 (2)0.0053 (19)0.0046 (19)
C70.044 (2)0.061 (3)0.050 (3)0.005 (2)0.0077 (19)0.002 (2)
C80.035 (2)0.048 (2)0.033 (2)0.0044 (16)0.0039 (16)0.0031 (18)
C90.045 (2)0.041 (2)0.033 (2)0.0053 (17)0.0099 (16)0.0047 (17)
C100.044 (2)0.053 (2)0.034 (2)0.0061 (18)0.0062 (18)0.0004 (19)
C110.044 (2)0.048 (2)0.038 (2)0.0033 (17)0.0098 (18)0.0040 (18)
C120.086 (4)0.090 (4)0.075 (4)0.029 (3)0.037 (3)0.009 (3)
C130.070 (3)0.061 (3)0.118 (5)0.012 (3)0.029 (3)0.012 (3)
C140.058 (3)0.085 (3)0.040 (3)0.018 (2)0.007 (2)0.003 (2)
C150.037 (2)0.050 (2)0.044 (2)0.0025 (17)0.0047 (18)0.0018 (19)
C160.041 (2)0.053 (3)0.052 (3)0.0024 (18)0.004 (2)0.006 (2)
C170.061 (3)0.070 (3)0.077 (4)0.001 (2)0.006 (3)0.018 (3)
C180.104 (4)0.080 (4)0.061 (3)0.000 (3)0.004 (3)0.020 (3)
C190.051 (3)0.102 (4)0.065 (4)0.011 (3)0.002 (2)0.012 (3)
Geometric parameters (Å, º) top
Si1—C111.832 (4)C7—H70.95
Si1—C121.847 (5)C8—C91.429 (5)
Si1—C131.847 (5)C8—C151.443 (5)
Si1—C141.850 (5)C10—C111.207 (5)
Si2—C161.835 (4)C12—H12A0.98
Si2—C191.847 (5)C12—H12B0.98
Si2—C181.853 (5)C12—H12C0.98
Si2—C171.854 (5)C13—H13A0.98
N1—C11.313 (5)C13—H13B0.98
N1—C91.372 (5)C13—H13C0.98
C1—C21.404 (5)C14—H14A0.98
C1—H10.95C14—H14B0.98
C2—C31.362 (5)C14—H14C0.98
C2—H20.95C15—C161.207 (5)
C3—C41.410 (5)C17—H17A0.98
C3—H30.95C17—H17B0.98
C4—C51.419 (5)C17—H17C0.98
C4—C91.432 (5)C18—H18A0.98
C5—C61.382 (5)C18—H18B0.98
C5—C101.446 (5)C18—H18C0.98
C6—C71.401 (5)C19—H19A0.98
C6—H60.95C19—H19B0.98
C7—C81.364 (5)C19—H19C0.98
C11—Si1—C12106.6 (2)C11—C10—C5174.3 (4)
C11—Si1—C13108.3 (2)C10—C11—Si1172.8 (4)
C12—Si1—C13110.5 (3)Si1—C12—H12A109.5
C11—Si1—C14109.85 (19)Si1—C12—H12B109.5
C12—Si1—C14107.8 (2)H12A—C12—H12B109.5
C13—Si1—C14113.5 (3)Si1—C12—H12C109.5
C16—Si2—C19106.6 (2)H12A—C12—H12C109.5
C16—Si2—C18109.0 (2)H12B—C12—H12C109.5
C19—Si2—C18111.7 (3)Si1—C13—H13A109.5
C16—Si2—C17108.9 (2)Si1—C13—H13B109.5
C19—Si2—C17111.0 (2)H13A—C13—H13B109.5
C18—Si2—C17109.5 (3)Si1—C13—H13C109.5
C1—N1—C9117.6 (3)H13A—C13—H13C109.5
N1—C1—C2124.7 (4)H13B—C13—H13C109.5
N1—C1—H1117.7Si1—C14—H14A109.5
C2—C1—H1117.7Si1—C14—H14B109.5
C3—C2—C1118.8 (4)H14A—C14—H14B109.5
C3—C2—H2120.6Si1—C14—H14C109.5
C1—C2—H2120.6H14A—C14—H14C109.5
C2—C3—C4119.6 (4)H14B—C14—H14C109.5
C2—C3—H3120.2C16—C15—C8176.1 (4)
C4—C3—H3120.2C15—C16—Si2176.8 (4)
C3—C4—C5123.2 (3)Si2—C17—H17A109.5
C3—C4—C9117.6 (4)Si2—C17—H17B109.5
C5—C4—C9119.2 (3)H17A—C17—H17B109.5
C6—C5—C4120.0 (4)Si2—C17—H17C109.5
C6—C5—C10121.5 (4)H17A—C17—H17C109.5
C4—C5—C10118.4 (3)H17B—C17—H17C109.5
C5—C6—C7120.3 (4)Si2—C18—H18A109.5
C5—C6—H6119.8Si2—C18—H18B109.5
C7—C6—H6119.8H18A—C18—H18B109.5
C8—C7—C6121.7 (4)Si2—C18—H18C109.5
C8—C7—H7119.1H18A—C18—H18C109.5
C6—C7—H7119.1H18B—C18—H18C109.5
C7—C8—C9119.7 (3)Si2—C19—H19A109.5
C7—C8—C15120.2 (4)Si2—C19—H19B109.5
C9—C8—C15120.1 (3)H19A—C19—H19B109.5
N1—C9—C8119.3 (3)Si2—C19—H19C109.5
N1—C9—C4121.8 (3)H19A—C19—H19C109.5
C8—C9—C4119.0 (4)H19B—C19—H19C109.5
C9—N1—C1—C21.9 (6)C6—C7—C8—C90.9 (6)
N1—C1—C2—C32.0 (6)C6—C7—C8—C15179.5 (4)
C1—C2—C3—C40.6 (6)C1—N1—C9—C8179.8 (4)
C2—C3—C4—C5178.6 (4)C1—N1—C9—C40.5 (5)
C2—C3—C4—C90.7 (5)C7—C8—C9—N1178.6 (4)
C3—C4—C5—C6178.5 (4)C15—C8—C9—N11.0 (5)
C9—C4—C5—C60.6 (6)C7—C8—C9—C41.1 (6)
C3—C4—C5—C101.0 (6)C15—C8—C9—C4179.3 (3)
C9—C4—C5—C10178.9 (3)C3—C4—C9—N10.7 (5)
C4—C5—C6—C70.4 (6)C5—C4—C9—N1178.7 (3)
C10—C5—C6—C7179.1 (4)C3—C4—C9—C8178.9 (3)
C5—C6—C7—C80.5 (7)C5—C4—C9—C81.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···N1i0.952.693.483 (5)141
C14—H14C···N1ii0.982.803.671 (6)149
Symmetry codes: (i) x, y1/2, z1/2; (ii) x+2, y, z.
 

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